Microsoft’s Big Ad Push Is the Latest of Its Brilliant Hits, Gnarly Misses

Right now Windows 8 and the Surface tablet probably rings a bell for every man, woman and child that walks, drives or skateboards through a major city. And if you don’t live the urban life, just turn on your television or fire up your laptop. Microsoft is on one of its periodic marketing binges, but this one, even by past comparisons, is a massive gut-buster. It’s estimated that the software giant is spending between $1.5 billion and $1.8 billion on television commercials and online and print advertisements.

It makes sense that Microsoft is pulling out all the stops. It desperately needs to prove that the Surface can compete with the iPad, and that Windows 8 Phones are just as good a choice as Android, or the iPhone, and, well, that Windows is still a great operating system.

But can spending big to unleash a flood of advertising really get consumers to give Microsoft’s new gadgets a second look? Paul Venables, co-founder of advertising firm Venables Bell & Partners, says it’s not about the cash; it’s about Microsoft clearly presenting its values to potential customers. “For years and years, Microsoft has always taken an overly rational and technical approach to selling its products,” says Venables. “But humans don’t buy on rational. They look for companies that share the same values as they do.”

That’s where Apple has succeeded and Microsoft has failed lately as it tries to play catch-up with its keenest competitor. For most of its existence, Microsoft was a company driven by software engineers selling software. That was fine when Windows ruled the world. But now iOS does. It's no surprise then, that as Microsoft tries to be a software, gadget, mobile, and cloud company, it’s having a hard time figuring out how to sell everything to everyone, says Venables. Take the Surface and Windows 8; there isn’t a clear audience or purpose. “We've seen ads full of music and dancing,” Venables says, “but little substance about why we should be forking over our money for Microsoft's new technology.” And at least for the "RT" version of the Surface tablet, not a whole lot of people have.

Looking back at Microsoft's early ads, this isn't the first time the company has struggled with explaining why anyone should open their wallets for its new tech. But for every bizarre ad, there are others that did a great job of getting people excited about Microsoft's latest technology. We’ve rounded up eight commercials from Microsoft's past and present: four cringe-worthy ads, and four that are as enjoyable to watch as any ad can be, starting with the video that launched Windows 95. Looking back at the hit campaigns and products, it’s easy to remember when the gang from Redmond was on top. They haven’t been there for a long time, which is why gadget-wise, and marketing-wise, more than ever Microsoft needs a hit.

Windows 95

Seventeen years after it aired, Windows 95’s classic ad still evokes the excitement people felt from getting their hands on Microsoft’s first window-based operating system. With the Rolling Stones' "Start Me Up" playing in the background, we see how lightning-fast Windows 95 could load programs and get online. Looking back, we know the system was not nearly as speedy as the ad, but it shows off the new possibilities of the Start Menu. More importantly, the video focuses almost entirely on how people everywhere, from young children to working adults, can use Windows 95. Microsoft wanted everyone to get on board with the new operating system, and the ad did a great job of showing that.

Future Windows ads weren't as empowering. The Windows 98 ad feels much too hectic, with quick cuts to different features of the operating system. For Windows XP, Microsoft showed people again, but this time they were flying through buildings and over a grassy hill. Microsoft spent $300 million on the launch of Windows 95, including ads. It was money well spent. By 1997, 77 million copies of the operating system were in use.

Bill Gates and Jerry Seinfeld

If there is a good explanation for this ad campaign, we can't think of it. A series of TV commercials that launched in 2008 kicked off with Jerry Seinfeld helping Bill Gates shop for a new pair of shoes. In follow-up ads, the pair is living with a “normal” family to connect with average users of Microsoft products. All three ads are plagued by an awkwardly long interaction between the two men, ending with a brief mention of the future of Microsoft. They might be funny, but none of the ads make sense, nor give you a clue of what Microsoft is trying to sell.

At the time, Microsoft was trying to boost its image following the release of Windows Vista. The ads were met with fierce criticism, with those in the tech community calling them a train wreck. Reportedly, Seinfeld was paid $10 million for the ads; the money could have been better spent calming angry Vista users with free smoothies or something.

'I'm a PC'

For Microsoft cheerleaders, this is a favorite ad campaign. In 2006, Apple gave us the "Get a Mac" campaign, which featured the popular "I'm a Mac, I'm a PC" videos. Actor Justin Long played the cool, hip Mac computer, and comedian John Hodgman was cast as an old, slow, and virus-ridden personal computer. The ads made Macs seem like all-around fun and stable machines, while PCs were boring, work-focused, and full of problems.

Microsoft didn't take that lying down. Though it took two years to retaliate, the company launched its "I'm a PC" campaign in 2008. The commercials showed a mix of celebrities, like Eva Longoria and Bill Gates, with average people talking about how they use their Windows computers to do work or other cool projects. Firing back at Apple, the beginning of the ad shows Microsoft employee Sean Siler dressed up like John Hodgman's character. The campaign cost Microsoft $300 million and was designed by the Crispin Porter + Bogusky agency. While it did nothing to stop Apple’s rocket-like ascent (they had moved on to the iPhone by then, while Microsoft was still stuck on the desktop), it did make Windows users feel better about themselves.

KIN

Microsoft's ads for its failure of a phone, the KIN, are a perfect example of what happens when you try to connect with your customers – in this case young adults – in exactly the wrong way. Every one of the commercials, the KIN phone, which launched in 2010, offended one group or another — and for good reason. One video, titled "Basement," showed a young guy taking a photo of his chest under his shirt and sending it to his social network. Cue the angry parents' groups who said the ad promoted "sexting," or sending nude photos with your phone.

Then, came the ads that highlighted the KIN's social networking feature, called Loop (remember that? didn’t think so). One video shows what looks like a teenage girl showing up at the door of a male Facebook friend she had never met before. When he turns out to look completely different than his photo, she snaps a picture and shares it with her Loop friends. You don't have to be a parent to feel horrified that Microsoft somehow was encouraging meeting up with complete strangers, even if it did so inadvertently.

Kinect

The Kinect might not be a favorite of hardcore gamers, but it doesn't seem like Microsoft was trying to reach that market when it launched the peripheral in 2010. The Kinect's first ad did an awesome job of getting the casual gamer, or anyone who has a game console in their home, to take notice of the Xbox.

Instead of using a controller, as the video shows, all you have do is to move your hand or body to control a game. If you just want to watch a movie, forget the remote – just say "Xbox Play" and the Kinect will understand you. The novelty of using your hands and body to control games and menus was a big hit, and made the Kinect a Guinness World Record holder for the fastest-selling consumer electronics device.

Internet Explorer

Internet Explorer has been one of the most disliked web browsers since the launch of IE 6 in 2001. As if the bugs and too-late fixes weren't enough, in 2009, Microsoft sullied Internet Explorer's hated image even more by giving us an ad with a woman puking on her husband after seeing his browsing history. The video was meant to highlight Internet Explorer 8's private browsing feature. Naturally, people were disgusted with the ad and Microsoft pulled it quickly after it launched it. However, it lives on forever thanks to YouTube.

Three years later, Microsoft has cleaned up IE's image and managed to make it actually cool. The company launched an ad this week with a hard-core IE troll who changes his tune after reading about the browser's accolades on Twitter and Facebook. He might still dislike Internet Explorer by the end of the ad, but at least he doesn't hate it. Microsoft calls that progress. We’re not so sure.

The Bing It On Challenge

You'll have probably seen this Pepsi Challenge for search engines, a video that launched in September 2012. In the "Bing It On Challenge" a guy asks people on the streets of San Francisco – Google's backyard, as he calls it – to do a side-by-side comparison of search results from Google and Bing. If Google wins, you get a free Xbox, if Bing wins, the host gets to keep your sweater or you have to walk across the street in your underwear. Wait, what? Of course, everyone in the ad, all former Google devotees, choose Bing. We just want to know how many Xboxes were given away off-camera.

Two months later, Bing decided to go after Google's jugular with the "Scroogled" videos. Microsoft points out that when you search for a product on Google, the top shopping results you get are really just paid ads. It's not exactly a shocking revelation, since we know that Google makes nearly all of its money from ad sales. It does, however, make Microsoft look petty while trying to promote their still-struggling search engine Bing.

Surface and Windows 8

In launching a new tablet, Microsoft has taken a few cues from its biggest mobile-computing competitor, Apple. While Apple has moved away from the music-video-style ads that showed off iTunes and the iPod, it looks like Microsoft just discovered that tactic.

The Surface ad plays like a heavily choreographed music video and shows off the satisfying clicks the tablet makes when you pop out the kickstand or attach the keyboard covers. However, Microsoft knows that to sell its tablet, it needs to prove the Surface is as useful as Google's Android line and as cool as the iPad. The Surface ad does neither.

Microsoft's Windows 8 ads aren't much better. Yes, they show off the nifty Picture as a Password feature, and the live-tiled Start Screen, but it's unclear if Microsoft is trying sell us some fun features, or a full-functioning operating system that's worth the upgrade. Windows 8 sales have missed the company's internal projections, as well as PC makers' projections, so it seems many people are still trying to figure that out too.